Smart Task, Seek non-brute force solution

I have a challenge that I'm trying to do in Smart Task. I can do this by brute force of some twenty different Smart Tasks, but I'm looking for a more elegant solution. And even so, I don't think I'll ever get it below even three, given the constraints of Smart Task. But I write, in hopes that one of you can offer some suggestions:

What I'm trying to do is: When I contract with a new client, there will be a term of engagement of some three months (or more or less), with a specific task weekly. Perhaps on some trigger such as New Opportunity (of specific process) with New Product, with engagement end date (perhaps Estimated Close Date), the process will begin automatically. I want to...

1) Generate a scheduled task to write the Engagement Letter from templates. (Sub-problem: I can't seem to automate this, at best doing a reminder task. If I link to the template, it opens the template, not the pre-filled letter.)

2) Schedule a task reminder (or better yet, generate the actual templated email) that will go out on weeks 1, 2, and 3.

3) Then, on the 4th week, Schedule a appointment reminder to meet with client.. --And all this will continue on this schedule until the engagement period is over.

So, automatic (or near) emails each week for three weeks, and a scheduled meeting for the fourth -- all to be repeated on some trigger to continue until an Estimated Close Date is reached.

I can create one Smart Task (and have it look at Est Close Date) for however many weeks out, but if the engagement goes on for a year, this gets ugly to have to program 52 of these things (most of which not ever triggering) for what will mostly be a three month engagement.